Tetrahedron letters

Efficient alkylsulfanyl (SMe, SEt and SCH 2 Ph) and sulfanyl (SH) migration in the stereospecific synthesis of substituted tetrahydrofurans

J Eames, RVH Jones, S Warren

Index: Eames, Jason; Jones, Ray V.H.; Warren, Stuart Tetrahedron Letters, 1996 , vol. 37, # 27 p. 4823 - 4826

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Citation Number: 18

Abstract

Treatment of a series of 4-RS-1, 3-diols (R= Me, Et, Bn and H) with TsOH in CH2Cl2 gives substituted tetrahydrofurans. We discuss the scope of this reaction using structural variation of the migrating (RS) substitutent. All reactions proceeed in high yield and give yield synthetically useful products.